First Ward Alderman in Chicago from 1893-1938. Coughlin received his nickname because he began working in Turkish bathhouses as a rubber, eventually owning his own tavern and bathhouses. Along with his partner, fellow first ward alderman "Hinky Dink" Kenna, Coughlin was known as the “Lords of the Levee,” a district included in their ward which provided them with the support of prostitutes, pimps, tavern-owners, and gamblers.

Coughlin was corrupt, but he had his limits. When transit magnate Charles Yerkes offered him a bribe to vote for Yerkess interests, Coughlin reported the incident to Mayor Carter Harrison, Jr., explaining that Yerkes had offered too much. Coughlin's attitude was you could get just as rich in the long run accepting small bribes with less of a chance of getting caught.

Coughlin and Kenna's best known activity was the first ward ball, an annual fundraiser which brought together safecrackers, prostitutes, politicians, businessmen, gamblers, and others. The event would raise more than $50,000 a year for the two first ward aldermen until it was closed down in 1909 by Mayor Fred Busse. By the time it ended, the ball had moved into the Chicago Coliseum and ended in annual riots.

When Coughlin was accused of corruption, he demanded a retraction, not for the charge of graft, but for the claim he was born in Waukegan, Illinois.

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